ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Piperidine → 4-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-(1,3-thiazol-2-yl)but-3-yn-2-ol

HRID 1398482
ノート
印刷プレビュー

反応式

HRID 1398482 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:18])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)=[CH:4][CH:3]=1.N1CCCCC1.[S:25]1[CH:29]=[CH:28][N:27]=[C:26]1[C:30]([OH:34])([C:32]#[CH:33])[CH3:31]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[NH2:17][C:13]1[N:12]=[C:11]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([C:33]#[C:32][C:30]([C:26]4[S:25][CH:29]=[CH:28][N:27]=4)([OH:34])[CH3:31])[CH:10]=3)[C:6]([CH3:18])=[N:7]2)[CH:16]=[CH:15][N:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8082PiperidineHCID 582215512-(Thiazol-2-yl)but-3-yn-2-olHCID 681818654-(6-bromo-3-methyl-1H-indazol-1-yl)pyrimidin-2-amine

生成物 1

HCID 601485364-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-(1,3-thiazol-2-yl)but-3-yn-2-ol

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
60 °C

実験手順

To a mixture of 4-(6-bromo-3-methyl-1H-indazol-1-yl)pyrimidin-2-amine (5-a) (240 mg, 0.489 mmol) and piperidine (1.2 mL) was added tetrakis(triphenylphosphine)palladium (53.5 mg, 0.049 mmol), copper(I) iodide (9.3 mg, 0.049 mmol) and 2-(1,3-thiazol-2-yl)but-3-yn-2-ol (I-1) (150 mg, 0.978 mmol). The reaction was purged with N2 and stirred at 60° C. for 1.5 hr. The reaction mixture was concentrated in vacuo. EtOAc (2 mL) was added to the residue and concentration in vacuo was repeated. The resultant residue was purified by flash chromatography (Isolute column, 100% DCM to 3% MeOH in DCM) to afford the title compound as a white solid: 1H NMR (250 MHz, DMSO) δ 1.87-1.97 (3H, m), 2.56 (3H, s), 6.91-7.00 (1H, m), 7.01-7.07 (1H, m), 7.10-7.23 (1H, m), 7.29-7.40 (1H, m), 7.65-7.73 (1H, m), 7.74-7.80 (1H, m), 7.81-7.90 (1H, m), 8.19-8.32 (1H, m), 8.76-8.92 (1H, m); LC-MS: m/z=+377.5 (M+H)+.

後処理

  1. customThe reaction was purged with N2
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionEtOAc (2 mL) was added to the residue and concentration in vacuo
  4. customThe resultant residue was purified by flash chromatography (Isolute column, 100% DCM to 3% MeOH in DCM)

出典と根拠

ORDレコード
ord-5f0f0a5d868d4a3c891e7c78d795e1cf
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901313B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート